In the previous post (Part 1), we explored some business questions you, the prospective CISO, should ask to truly grasp the organization’s landscape and set yourself up for success. In this part we will focus on questions about the position itself.
This is important because the previous questions were understanding the company’s DNA, and gain understanding if the organization and its culture are the right fit for you. The following questions are diving into the position itself and ideally this conversation should happen with your future boss.
You will need to listen very carefully because in addition to the role and requirement of the role, there may be some history there that will be very valuable to learn from. Ultimately, you are trying to determine if this is the right fit for all parties.
Questions about the CISO position
Scope
- What organizations, functions, and assets fall under the CISO’s umbrella?
Does it cover the organization internally or extend to subsidiaries and other external parties? Knowing the scope is key to planning and resource allocation - Is the focus solely on cyber security, or does it encompass physical security, data privacy, and compliance? A broader scope requires a diverse skillset and strategic thinking.
The ideal CISO
- What specific qualities, skills, and experience are you seeking in your next CISO? Understanding their expectations helps you showcase relevant strengths as well as identify gaps.
- Is the organization looking for a seasoned veteran or someone with growth potential? This helps clarifies your potential career trajectory within the organization.
Measuring Success
- What are the specific milestones or metrics by which this role’s success will be evaluated? Clarity on performance expectations is key. Knowing the benchmarks will help you set goals and track your progress effectively.
- How will I know if I’m making a positive impact? This will help you understand whether the organization has a clear vision for the role or not.
- How does the organization measure the effectiveness of its security program? Knowing how the organization evaluates its security program reveals their priorities and expectations for you. If they lack clear metrics, it indicates a potential lack of commitment to security or an undefined vision. This could pose challenges in aligning your efforts with their needs.
THe CISO place in the Hierarchy
- To whom will the CISO be reporting? Understanding your reporting line determines your level of autonomy and influence. You will also want to understand how the business unit you will be part of interact with other units.
- What is the decision-making process for security initiatives? Will you have a seat at the strategic table, or will you be implementing decisions made elsewhere? Also, who will be your champion or sponsor?
Challenges
- What do you see as the biggest challenges or roadblocks I might face in this role? This reveals potential obstacles and allows you to assess your fit and readiness to tackle them. Also, Proactively discussing potential hurdles demonstrates your ability to anticipate and overcome difficulties.
- What resources and support will be available to overcome these challenges? Understanding the support system shows the organization’s commitment to the security practice and to your success.
Incidents
- How does the organization handle security incidents? Their incident response process reveals their readiness and culture in handling security breaches. A weak or ill-defined incident response process suggests potential vulnerabilities in their overall security posture.
- Can you describe the most significant cybersecurity incident you’ve faced in the past [x years] and what were the key lessons learned? The answer reveals response capability, learning culture, and communication practices.
Partnerships
- Which stakeholders are critical for the CISO to partner with for success? Identifying key partners will help you build strong relationships and leverage diverse perspectives.
- How does the organization foster communication and collaboration between security and other departments? A strong security culture depends on open communication and cooperation.
Learnings from past experiences
- “Can you share any past experiences or challenges faced by the previous CISO in this role? How were these addressed, and what lessons were learned?” Understanding the history of the position can provide valuable insights into the organizational culture and potential roadblocks.
Available Resources
- “What resources, budget, and team support will be available to me in this role? This answer will be very different whether you need to build everything from the ground up or join an already established practice.
- How can I effectively utilize these resources to achieve the desired security outcomes?” Knowing the available tools and support will help you develop a realistic and achievable security strategy.
Conclusion
These questions are just the starting point for the conversation. Be an active listener, probe deeper, and don’t hesitate to ask follow-up questions. This is your chance to not only learn about the role but also to showcase your own leadership, strategic thinking, and communication skills. By approaching the interview with a proactive and insightful mindset, you’ll not only navigate the unknown but also demonstrate your potential as the CISO who can truly partner and empower the organization from within.
What other questions about the role did you find helpful to ask in your interviews? I would love to hear from you.
